Risk of being "On the Fly" for 20 Day Trip Portugal

Posted by jeffbkrause123 on 03/29/25 08:27 PM

It is a last minute opportunity for my wife and I to travel to Portugal for 20 days (June 1 - June 20). Your thoughts appreciated about being flexible with our accommodations. e.g. Don't pre-book hotels, rather depending on where we travel to using a car, be spontaneous. Book accommodations a day or two in advance while we are traveling.

We currently have three nights in Lisbon booked. Then after that no specific hotel/accommodations reservations. Is it too risky to try to be flexible this time of year?

Your thoughts appreciated.

Posted by Jazz+Travels

Chicago

03/29/25 08:35 PM

8338 posts

Not risky, the only negatives are that lodging can be more expensive booked last minute and you could lose time researching trying to decide where you want
to stay; I travel like this most of the time.

Posted by funpig

Vancouver, BC, Canada

03/30/25 10:03 PM

1445 posts

jeffkrause123

I haven't done anything like that in more than 30 years. As long as the both of you share this carefree and spontaneous attitude, you should be fine. It's always possible to find somewhere to sleep. However, if your wife is of a different mindset, be prepared for marital strife, or some really expensive stays and dinners to make up for any disappointments along the way.

Posted by Lisa

Calgary, AB, Canada

04/01/25 12:40 AM

606 posts

We have done a modified version of this twice in Portugal, but it was in April both times. Things to watch out for are holiday weekends. A quick look shows a couple of potential holidays ( June 10 and June 13). I would want to find out if the Portuguese would be holidaying the same time, and book those dates.
I also tend to book the end of the trip, as well as any bigger cities where location is important and where a last minute hotel might be very costly.
And then there is the unexpected. A marathon in Coimbra left us with a choice of a hostel, or the most expensive hotel in town. We picked the hostel ( private room) and it was great, but you never know...

Posted by jeffbkrause123 OP

04/01/25 03:24 PM

2 posts

Thank you for the suggestions! Based on your suggestions: best that we do a hybrid travel of "on the fly" and pre-booking. Taking your advice roughed in the itinerary below:

3 nights (booked) in Lisbon.
Pick up rental car day 5 in Lisbon, head south to Lagos.
Lagos (booked 4 nights), explore the Algarve area with day trips.
Then (1 - 4 nights) the "on the fly" part: head north up the coast perhaps a mix of overnights or just stop-ins at Sines, Nazare, Tomar, with a next hub destination Coimbra.
Coimbra (will book 2- 4 nights) and will use as a hub for day visits to central locations
Porto (will book) 3 nights.
Back to Lisbon (book 1 night) near airport
Rental return, fly out for the Barcelona leg of the trip.

Any additional thoughts appreciated. Thank you.